CUBEBiE. .587 



Chemical Composition — The most obvious constituent of cubcbs 

 is the volatile oil, the proportion of which yielded by the drug varies 

 from 4 to 13 per cent. The causes of this great variation may be found 

 in the constitution of the drug itself, as well as in the altcrabihty of t lie 

 oil, and the fact that its prevailing constituents begin not to bitil 

 below 2G4<^ C. It is, as shoAvn in 1875 by Oglialoro, a mixture of an oil 

 C^"H^^, boiling at 158''-163'', which is present to a very small amount, 

 and two oils of the formula 0'iV\ boiling at 202-205^ C. One of the 

 latter deviates the place of polarization strongly to the left, and yields 

 the crystallized compound a'H"' 2 HCl, melting at 118^ C. The other 

 hydrocarbon is less laevogyrate and cannot be combined with HCl 



One part of oil of cubebs, diluted with about 20 parts of bisulphide 

 of carbon, assumes at first a greenish, and afterwards a blue coloration, 



' ' ' ic and nitric acids 



if one drop of a mixture of concentrated sulphuri 

 (equal weight of each acid) is shaken with the soluti 



solution. 



The oil distilled from old cubebs on cooling at length deposits largo, 

 transparent, inodorous octohedra of camphor of ciihehs, C^H*+2 01 P, 

 belonging to the rhombic system. They melt at 65° and may be 

 sublimed at 148°. We have not succeeded in obtaining them by keeping 

 the oil of fresh cubebs for two years in contact with Avater, to which a 

 little alcohol and nitric acid was added. 



Another constituent of cubebs is Guhehin, crystals of which may 



■J 



o 



boiling 



alcohol, but is mostly deposited upon cooling; it requires 30 parts of coir] 

 ether for solution, and is also abundantly soluble iu chloroform.^ \\ c 

 found this solution to be slightly la^vogyre ; it turns red on addition ot 

 concentrated sulphuric acid. If the solution of cubebni ni chlorotorm is 

 shaken with dry pe'ntoxide of phosphorus, it turns Um and graduaUy 

 becomes red by the influence of moisture. Cubebin is nearly insoluble in 

 cold, but slightly soluble in hot water. Bernatzik (1S66) obtained fr(.m 

 cubebs 0-40 per cent, of cubebin, Schmidt (1870) 2-5 per cent. Ibe 

 crystals, which are deposited in an alcoholic or ethereal extract oi 

 cubebs, consist of cubebin in an impure state. Cubcbm is devoid or 

 any remarkable therapeutic action. Its composition, according to 

 Weidel (1877) answers to the formula C^H^O^; by melting it with 

 caustic potash, cubebin is resolved as follows : 



Acetic Ackl. Protocatcchuic Acid. 



The resin extracted from cubebs consists ofan /"^f^'f/ I'^'^;:"' 

 nearly 3 per cent., and of Cahchlc Acid, amounting to ^:^<?;;^ , /'"\ '\^^'^ 

 of the drug. Both are amorphous, and so, according to fecli mid , a. e the 

 salts of cubebic acid. Bernatzic however, found some of them as that 



cubebic 



of barium, to be crystallizable. Schulze (187:3) prepaid cuucoi. ..^ 

 from the crystallized sodium-salt, but was unable to go toU^^^^^^^ 

 amorphous. The resins, the indifferent as well as the acid, possess the 



therapeutic properties of the drug. . •, i „f „„n-. (R nor 



Schmidt further pointed out the presence m cubebs, of gum (8 per 

 cent.), fatty oil, and malates of magnesium and calcium. 



